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Set on over 1.4 acres in one of Milton's most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn-offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

More Info

Basic Information

  • Bedrooms3
  • Mls StatusNew
  • Bathroom3
  • Parcel Number M:J B:014 L:8,133098

Tax Information

  • Tax Assessed Value $1,431,900
  • Tax Year 2025
  • Taxes$15,880

Parking

  • Parking Spaces10
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Detached, Paved Drive

Rooms

  • Bathroom 1 First
  • Bathroom 2 Second
  • Bathroom 3 Second
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Dining Room First
  • Family Room First
  • Full Bath2
  • Half Baths1
  • Kitchen First
  • Living Room First
  • Master Bedroom Second
  • Office First

Basic Information

  • List Price$1,895,000
  • MLS Number73523755
  • Modification Date05/26/2026
  • Property SubTypeSingle Family Residence

Location

  • Address268 Highland Street
  • Building Number268
  • CountyNorfolk
  • StateMA
  • StreetHighland Street
  • TownMilton
  • Zip02186

Building

  • BasementPartially Finished
  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplace Features Family Room, Living Room
  • Fireplaces Total 3
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Patio
  • Property StyleColonial
  • Rooms9
  • Year Built1938
  • Year Built Details Actual
  • Year Built Source Public Records

Property

  • Acreage1.4
  • Other Structures Barn/Stable

Interior

  • Interior Features Home Office, Bonus Room, Wet Bar

Exterior

  • Exterior Features Patio, Rain Gutters, Barn/Stable, Professional Landscaping, Sprinkler System
  • RoofSlate

Utilities

  • Cooling Central Air, Ductless
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Baseboard, Natural Gas, Fireplace
  • Sewer Public Sewer
  • Water Source Public

Property Information

  • Square Feet2,987
  • Building Area Source Public Records
  • Living Area 2,987
  • Lot Size Square Feet 60,949
  • Lot Size Units Acres

Amenities

  • Appliances IncludedOven, Dishwasher, Disposal, Range, Refrigerator

Legal

  • ZoningRA

Other

  • Date Listed05/26/2026
  • Farm Land Area Units Square Feet
  • View Count2

Map Location

Driving Directions

Listed by Beth Rooney of eXp Realty

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